All characters (that have sex) in this story are at least 18.
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To me, my stepmom (we'll call her Debbie) is fairly average - nothing I thought any of my friends would call a MILF - probably really cute when she was younger. (A 7 out of ten maybe?) She was, however, very nice, doing all the things a kid like me could ask for from a mom. And she liked it whenever I had friends over after school.
All through school, I was never very popular and only had one or two friends that only visited occasionally. In my senior year, however, as we all started turning 18, I began to have more and more guys befriend me and join what became a regular study and gaming group at my house. We would all do our homework and studying together, then most of us would all go jump on the game systems, taking turns gaming. Those that were waiting their turns usually ended up discussing video games and movies or playing cards around the dining table.
It all started about half-way into the school year, when I commented to my stepmom, that both of my friends had turned 18 this last weekend and wasn't that a cool coincidence. She got this odd look in her eye and asked, "Aren't you turning 18 next week?" I knew she knew when my birthday was.
Once we'd finished our homework, the three of us decided to take turns on a one-on-one fighting game, leaving Mike out for now. Debbie asked Mike if he could help her reach something for her, and we didn't see him until just before his turn on the game. He seemed to be a bit unfocussed, but he snapped out of it pretty quick as he and I battled.
I didn't notice Jeff's absence until it was time to switch again. He came out of the back hallway, a bit unfocussed, like Mike. "Are you okay? What were you doing?"
"I was just helping your mom put something away. I'm fine. Is it my turn again?" And nothing more was said.
Thinking back on it, this seemed to happen every time my friends came over, which now was every day, not just a few times a week. Soon, some of my other friends started coming over, too. This is how the group grew, as I'd described above. Debbie was very interested in how old each of my friends were and seemed to need a lot of help with various projects in the back of the house and garage. Every time she needed help, she would ask a different guy to help her (never me, though, as she explained I was the host and should always tend to my guests), so that just about everyone had helped her with some small task by the time they left. She even made it a rule that only guys that had turned 18 could help her - for "insurance purposes," as she put it.
A few months in, my dad went on a business trip, and Debbie commented at dinner, that I was the man of the house until he got back. We laughed and she asked me if I wanted some wine. Like any kid, I'd tried alcohol on the sly - one time I snuck a beer out to the back yard, and couple of times my friends and I had snuck a bit of whiskey. But this would be my first time with wine, so I said yes and she poured me a glass. I liked it a lot more than the other stuff I'd tried.
We talked and drank wine through dinner, then took more wine out to the living room and sat on the couch, me pretending to be an adult and enjoying myself to no end. I vaguely noticed that each time she got up to do something, she'd sit a bit closer, but didn't give it much thought. I was feeling mellow and enjoying talking to her like this, as she and I had never really talked much before. I started to understand why my dad had been attracted to her. She was very easy to talk to. Sooner than I'd realized, she and I had cuddled up close to each other. I commented that this was nice, admitting I was very awkward with girls. Before I realized what I'd just told her and gotten embarrassed, cuddling close was her favorite thing.